Shelter Island Vacations from ₩1,007,504

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The Latest Shelter Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
Price was ₩1,358,706, price is now ₩1,007,504 per person
₩1,007,504
per person
May 29 - Jun 1
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,031 reviews)
The rooms On the street are a bit loud. Cannot sleep in for sure. Otherwise great

Reviewed on Apr 16, 2026

Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was ₩1,426,274, price is now ₩1,014,069 per person
₩1,014,069
per person
May 29 - Jun 1
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (7,108 reviews)
The location was absolutely amazing. Close to everything. It also felt very safe. The rooms were clean and the house keepers and receptionist were amazing. A little old and small, but overall a great place to stay!

Reviewed on Apr 17, 2026

Tempo by Hilton New York Times Square

Tempo by Hilton New York Times Square

4 out of 5
Manhattan
Price was ₩1,616,326, price is now ₩1,206,029 per person
₩1,206,029
per person
May 29 - Jun 1
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (5,525 reviews)
Great location, clean hotel, and friendly staff.

Reviewed on Apr 15, 2026

Chelsea Savoy Hotel

Chelsea Savoy Hotel

2 out of 5
Manhattan
Price was ₩1,433,032, price is now ₩1,077,498 per person
₩1,077,498
per person
May 29 - Jun 1
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (2,456 reviews)
Clean room, friendly staff.

Reviewed on Apr 16, 2026

Arlo Midtown

Arlo Midtown

4 out of 5
Manhattan
Price was ₩1,443,170, price is now ₩1,109,604 per person
₩1,109,604
per person
May 29 - Jun 1
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (5,976 reviews)
Great stay, lots of elevators!

Reviewed on Apr 16, 2026

Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island
Center console boat on Long Island, NY. Photographed by drone.

Silver Beach

While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Crescent Beach.

Find hotels in Silver Beach

Find the Best Shelter Island Vacation Packages

Shelter Island Beach Vacation

There's nothing like a Shelter Island vacation to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town center on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometers away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.

Shelter Island Hotel Deals

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
The price is ₩858,284 per night from Apr 30 to May 1
₩858,284
₩1,176,707 total
Apr 30 - May 1
includes taxes & fees
8.4/10 Very Good! (754 reviews)
Our family of four stayed for 3 nights in a two bedroom suite with ocean views. We booked it last minute for spring break. Overall, we had an amazing time and enjoyed our stay despite the cold temps. The room was clean. I saw no obvious signs of aging of furniture, fittings and walls - a huge plus ...

Reviewed on Apr 14, 2026

Gurney's Montauk Resort & Seawater Spa
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
The price is ₩198,885 per night from Apr 20 to Apr 21
₩198,885
₩256,197 total
Apr 20 - Apr 21
includes taxes & fees
9.2/10 Wonderful! (1,324 reviews)
The kitchen was perfect, only thing missing was utensils. There is a local store on the way to the manor to pick some of those staples up from.

Reviewed on Apr 13, 2026

Montauk Manor
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
Fully refundableReserve now, pay when you stay
The price is ₩235,288 per night from Apr 19 to Apr 20
₩235,288
₩270,296 total
Apr 19 - Apr 20
includes taxes & fees
9.6/10 Exceptional! (463 reviews)
The hotel is clean

Reviewed on Apr 16, 2026

The Bentley Hotel Southampton
See all 4,737 properties in Shelter Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in Shelter Island

Havens House

You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.

Havens House

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.